title: Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction.
abstract: The design and synthesis of a new class of laser light activatable tetrazoles with extended π-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M(-1) s(-1). The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.
authors.affiliation: Department of Chemistry, State University of New York at Buffalo , Buffalo, New York 14260-3000, United States.
authors.forename: Peng
authors.initials: P
authors.lastname: An
authors.forename: Zhipeng
authors.initials: Z
authors.lastname: Yu
authors.forename: Qing
authors.initials: Q
authors.lastname: Lin
mesh_terms: D000475:Alkenes / Q000032:analysis / Q000737:chemistry*; D061565:Cycloaddition Reaction; D005456:Fluorescent Dyes / Q000737:chemistry*; D007834:Lasers; D008027:Light; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D005456:Fluorescent Dyes; D012997:Solvents; D013777:Tetrazoles